A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives.
The raise in clinical significance of multidrug-resistant bacterial pathogens has directed us to synthesize 2,6-diarylpiperidin-4-one and Delta(3)-tetrahydropyridin-4-ol based benzimidazole and O-arylsulfonyl derivatives. X-ray crystal structure of tetrahydropyridinol (23) confirmed a change in conformation and orientation of substituents upon amide formation. Antibacterial activities evaluated against a wide number of bacterial pathogens (both sensitive and multidrug-resistant) revealed that 19, 27 against Staphylococcus aureus, 27 against Enterococcus faecalis, and 19, 21, 23, and 27 against Enterococcus faecium are significantly good at lowest MIC(90) (16 microg/mL). Inhibitory power noticed by 23 against Vancomycin-Linezolid-resistant E. faecalis and 27 against Vancomycin-resistant E. faecium are onefold better than the standard Linezolid and Trovafloxacin drugs, respectively. Moreover, antitubercular activity for the selected compounds against Mycobacterium tuberculosis H37Rv revealed that compounds 23, 24, and 27 expressed onefold improved potency compared to the standard Rifampicin drug.
Aridoss
Gopalakrishnan
G
Division of Image Science and Information Engineering, Pukyong National University, Busan 608-739, Republic of Korea.
Amirthaganesan
Shanmugasundaram
S
Kumar
Nanjundan Ashok
NA
Kim
Jong Tae
JT
Lim
Kwon Taek
KT
Kabilan
Senthamaraikannan
S
Jeong
Yeon Tae
YT
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods; D018360:Crystallography, X-Ray / Q000379:methods; D015195:Drug Design; D004352:Drug Resistance, Microbial; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008956:Models, Chemical; D008958:Models, Molecular; D010880:Piperidines / Q000737:chemistry*; D010881:Piperidones / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012293:Rifampin / Q000138:chemical synthesis / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000995:Antitubercular Agents; D010880:Piperidines; D010881:Piperidones; D011725:Pyridines; D012293:Rifampin